Michael Sullivan

IT Executive. System Builder. Entrepreneur.

Michael Sullivan

I help growing companies turn technology from a bottleneck or a risk into an advantage.

I bring 30+ years in technology and 17 years running a successful technology business. I can sit with a leadership team, set the direction, and still know exactly what it takes to deliver it.

Get in touch View my LinkedIn profile
Portrait of Michael Sullivan
Cover of The Book of Possibility

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The Book of Possibility

by Jim Curtis

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30+years in technology
17years running my own technology business
~$300Mrevenue, up from $90M, at a company I helped grow
20+person teams built and led

Built from the ground up

I came up the hard way. I started in 1996 as a network and systems engineer, moved into running IT for a growing company, and helped it grow revenue more than 330%. In 2009 I started my own business so I could own the whole picture for the companies I serve: strategy, budget, infrastructure, security, compliance, and the vendors behind all of it.

Before technology, I played Division I baseball. That is where I learned what I still believe. Teams win on mental toughness and a refusal to accept mediocrity. They win on preparation, accountability, and doing the simple things right every day. The drivers are the pursuit of excellence and consistent progress. I run my work the same way, with a clear plan, a weekly rhythm, and a scorecard everyone can see.

Companies call me when technology has become a bottleneck or a risk. They keep me because I turn it into an advantage.

How I work

Four steps, in this order, every time.

  1. I

    Simplify

    Complexity is what makes IT expensive and fragile. I take it out first.

  2. II

    Standardize

    One way of doing things, documented, so it works the same every time.

  3. III

    Automate

    Then I automate what is left, so people spend time on work that matters.

  4. IV

    Innovate

    Now you have a foundation that can hold weight. That is where you build.

Where I help

IT leadership and strategy

Executive-level technology leadership for companies of 10 to 500 people. A roadmap and budget tied to business outcomes, and the follow-through to deliver it.

Cybersecurity and cyber insurance readiness

Incident response, compliance (HIPAA, NIST, ISO 27001), and hardened Microsoft 365, Azure, and Entra ID. I make sure you actually have the controls your insurance renewal requires.

AI and automation

Practical AI and automation that removes manual work and cost, built on top of a clean, standardized foundation.

Vendors, MSPs, and contracts

Vendor selection, contract negotiation, and MSP oversight, so you pay for results instead of activity.

Results

$90M to just under $300M
Helped drive this growth by improving the user experience, aligning technology with business tools, and leading simplification, standardization, automation, and innovation.
$3.5M to over $12M
Helped multiple organizations make this jump, with a much stronger partner, user, and client experience along the way.
4X revenue, 3.5X MRR
Led a full transformation of a managed services business, rebuilt the security stack, and turned around a 20+ person team.
330%+ revenue growth
Led a mobility-first technology strategy as Manager of IT for a growing company.
$1M+ saved
Cut litigation costs through an eDiscovery program.
39% lower IT operating costs
Plus 20% lower software licensing and 90% lower remote support and training costs.
24-hour remote workforce
Moved AEC, pharma, financial, and manufacturing clients to secure remote work within a day during COVID-19.

Industries served: Healthcare, Manufacturing, Professional services, Legal, Education, Architecture and engineering, Financial, Government.

Everyone else is playing checkers, and you’re playing chess.
Billy K.
Michael was always reliable, composed and proactive. He has that important blend of technical and interpersonal skills that make him an asset to any firm. I could always count on Michael and would feel fortunate to work with him again.
Angelo S.Chief Operating Officer
The project was a success, and it was completed ahead of schedule and under budget. This never would have been possible without Michael’s expertise, knowledge, and leadership.
Phil S.Principal Software Engineer
Michael is that one in a million person that every client, co-worker, or employer hopes to work with. He gives every avenue of his life 100% effort.
Robert M.Worldwide Account Manager
Creative, inspiring, empowering, and forward-thinking... Michael’s colleagues know that he values every one of them and their contributions to the overall success of the organization.
David H.Account Manager
He has a keen sense of technological direction and best practices to ensure efficient and cost effective IT management. Mike always kept the best interests of the company in mind.
Michael E.Enterprise Sales and Business Development
Michael Sullivan is a top notch IT professional. He is always well prepared, honest, and is very personable.
Chris F.National Recruiting Manager
He tackles all projects head-on and has a unique ability to juggle several of them simultaneously. In addition, his communication skills are top-notch.
Jim F.Senior Account Executive
His approach is prompt, courteous, and very professional.
John P.Principal Solutions Architect

Career

  1. 2009 to presentFounder and PrincipalSullivan-Solutions LLC
  2. 2020 to 2024Director of Client SolutionsACS Services, Inc.
  3. 2019 to 2020vCIOFocus Technology Solutions
  4. 2010 to 2016Executive Consultant and Enterprise ArchitectCustom Computer Specialists
  5. 2010Senior Global Systems ConsultantPegasystems
  6. 2003 to 2009Manager of Information TechnologyThe Computer Merchant, Ltd.
  7. 1996 to 2002Network and Systems EngineerStarlight Medical Logistics, Inc.

Education

  • B.S., Information Systems SecurityITT Technical Institute
  • A.A.S., Computer Network SystemsITT Technical Institute
  • IT certificate programsClark University, Computer Career Institute
  • Boston College High School

Certifications

  • CompTIA A+
  • CompTIA Network+
  • CompTIA IT Operations Specialist (CIOS)
  • Leveraging AI in Your Nonprofit Role (Microsoft and NetHope)

What I’m building

  • Sullivan-Solutions LLC

    IT leadership, cybersecurity, cyber insurance readiness, and AI services for growing companies.

    Visit site

  • Sullivan Capital Strategies

    Investment and tax strategy across crypto, forex, options, commercial real estate, and vehicles, built to lower your tax burden and strengthen your portfolio.

  • Play Better Solutions

    Gamified team platforms that put the coach’s playbook in every player’s hands. Messages, signs, and plays become something players want to log into, learn from, and enjoy, backed by best-in-class practice drill recommendations.

  • Forge Fire Protocol

    A podcast and business platform co-founded by Don, Mike, and Steve. Forged in Fire. Built for Legacy.

  • RFR Connect

    A referral networking group built to drive high-quality business leads.

  • Life Better Solutions

    Wellness and mindset improvement.

  • Everyday Renewable

    Solar for homes and businesses.

  • Agent SPT

    An AI chatbot that finds savings on utilities, payroll, and benefits.

  • Allied Resiliency

    Utility optimization and resiliency outreach.

  • Sullivan Family Foundation

    Newly founded and built for generations. We help families reach the education, funding, and elite athletic training they could not access on their own, and we champion education and excellence around the world.

Outside of work

Coach

I coach an 18U girls travel softball team and have coached for 15 years at the youth, travel, and club levels.

Athlete

Former Division I baseball player.

Family

Husband and father of four. Everything I build is for them.

Reader

Personal development is a daily habit. I share the books that shaped me and a pick every month.

Let’s talk.

If technology is slowing your company down or keeping you up at night, send me a note. I read every message and reply personally.